Flame retardant compositions utilizing amino condensation compounds

ABSTRACT

Flame retardant compositions of this invention are produced by incorporating an amino condensation compound or composition in a more flammable organic compound. The amino condensation compounds and compositions are produced by heating urea or heating urea with other nitrogen containing compounds that will condensate with or react with isocyanic acid and/or cyanic acid or heating urea first then reacting the condensation compounds with other nitrogen containing compounds. The amino condensation compounds may be mixed with or reacted with carbonization auxiliaries, aldehydes and mixed with fillers to produce an amino condensation composition which is incorporated in more flammable organic compositions such as polyurethanes, polyester resins, epoxy resins, vinyl resins and other resins. The amino condensation salts of phosphorus, boron or sulfur containing compounds and the amino condensation-aldehyde resins may also be used as the flame retardant compound in this invention. For example, polyurethane foams can be rendered less flammable with the amino condensation compounds or compositions and utilized as insulating materials.

This application is a continuation in part of Ser. No. 08/801,776, filedFeb. 14, 1997, now U.S. Pat. No. 5,788,915, which is a division of Ser.No. 08/723,779, filed Sep. 30, 1996, now U.S. Pat. No. 5,854,309.

FIELD

The invention concerns urea being condensated with other organiccompounds with a plurality of nitrogen atoms such as amino compounds toproduce amino condensation compounds. The invention also concerns theirpreparation and use. The amino condensation compounds are useful toproduce flame retardant plastics and flame retard natural products, andmay be reacted with phosphorus and/or boron containing compounds toproduce other flame retardant compounds. The amino condensationcompounds may also be reacted with aldehydes to produce aminocondensation-aldehyde resins for use as molding compounds or as a flameretardant compound.

BACKGROUND

The heating of urea to produce urea condensation compounds, such as amixture of cyanuric acid and cyamelide, is known in the arts, but theuse of these compounds as a flame retardant is novel. The condensationof isocyanuric acid and/or cyanic acid, (which are produced by heatingurea),with other nitrogen containing compounds to produce flameretardant compounds is novel. The amino condensation compounds and theirphosphorus and/or boron salts are used as flame retardant compounds inplastics and natural products. Urea and melamine were utilized as aflame retardant compound by Fracalossi, et al., in U.S. Pat. No.4,385,131. Melamine was utilized as flame retardant compounds inpolyurethanes by Yukuta, et al., in U.S. Pat. No. 4,221,875 and byGrinbergs et al., in U.S. Pat. No. 4,745,133. Amino phosphates wasutilized by Blount in U.S. Pat. No. 5,010,113.

What is lacking and what is needed are useful inexpensive nitrogencontaining organic compounds with a plurality of nitrogen moieties. Theamino condensation compounds and/or their salts of this invention arenovel flame retardant compounds. The amino condensation compounds suchas urea condensation compounds, urea-melamine condensation compound,urea-dicyandiamide compounds, urea-guanidine condensation compounds,etc., are novel flame retardant compounds. What is additionally lackingare compositions having such amino condensation compounds and/or theirsalts employed therein.

SUMMARY

In one aspect, the invention comprises amino condensation compounds andtheir salts.

Another aspect of the invention is a process to prepare aminocondensation compound and/or their salts comprising serially contacting

(A) urea

(B) nitrogen containing compound containing free NH₂—COOH, —OH, —NCOand/or epoxide radicals that will condensate or react with urea;

under conditions sufficient to prepare the amino condensation compounds.The urea may be first reacted with itself then reacted with Component Bor with more urea plus Component B or with Component B.

In another aspect, the invention comprises amino condensation salt ofphosphorus and/or boron containing compound and a process to prepare aamino condensation salt of a phosphorus and/or boron containingcompound, employing phosphorus and/or boron containing compound thatwill react with the amino condensation compound under conditionssufficient to prepare the amino condensation salt of a phosphorus and/orboron containing compound, and a process to prepare an aminocondensation salts of a phosphorus and/or a boron containing compoundcomprising serially contacting

(A) urea;

(B) nitrogen containing compound containing reactive —NH₂, —COOH, —OH,—NCO and/or epoxide radicals that will condensate or react with urea;

Components A and B are first reacted to produce an amino condensationcompound then a phosphorus and/or boron containing compound that willreact with an amino condensation compound is added mixed and reacted.

An addition aspect of this invention is the production of aminocondensation-aldehyde resins and a process to prepare aminocondensation-aldehyde resinous compound under conditions sufficient toprepare the amino condensation-aldehyde resin comprising seriallycontacting

(A) urea;

(B) nitrogen containing compound containing reactive —NH₂, —COOH, —OH,—NCO and/or epoxide radicals that will condensate or react with urea;

Components A and B are reacted thereby producing an amino condensationcompound then

(C) aldehyde;

(D) basic or acidic catalyst, are added and reacted.

An additional aspect of this invention is the production of flameretardant amino condensation compositions by mixing together thefollowing components

A) amino condensation compound and/or amino condensation salt of aphosphorus and/or boron containing compound and/or aminocondensation-aldehyde resin;

B) carbonization auxiliaries;

C) filler.

An additional aspect of the invention is the use of the aminocondensation compounds in the production of flame retardant aminocondensation salts of phosphorus and/or boron compounds, in theproduction of amino condensation-aldehyde resins and in the productionof amino condensation compositions. The flame retardant use comprisescontacting an otherwise more flammable organic material with the aminocondensation compounds and/or amino condensation salts of phosphorusand/or boron containing compounds and/or amino condensation-aldehyderesins and/or amino condensation composition thereof under conditionssufficient to lower the combustibility of the otherwise more flammableorganic material, for example plastics, natural products orpolyurethanes. Thus, a further aspect of the invention is aflame-retardant composition comprising an otherwise more flammableorganic material incorporated therewith a flame retardant amount of anamino condensation compound and/or a amino condensation salt of aphosphorus and/or boron containing compound, and/or aminocondensation-aldehyde resin, carbonization auxiliaries and fillers.

The flame-retardant compounds of this invention are produced by heatingurea (Component A) with a nitrogen containing compound (Component B) toabove the melting point of urea to about 160 degree C. at ambient orincreased pressure for 1-3 hrs. Upon heating above the melting point,urea form very reactive compound isocyanic acid and/or cyanic acid whichwill react with itself many times to form large molecules of cyamelideor with other organic or inorganic nitrogen containing compoundsespecially amino compounds. The condensation of urea by heating isillustrated as follows:

H₂NCONH₂→NH₃+HN═C═O⇄N═COH

wherein x is a number 3 to 10.

In order to increase the flame retardant properties and carbonizationproperties of the amino condensation compound a carbonization auxiliary,such as, phosphorus acidic compounds, organic phosphorus compounds thatwill react with an amino compound, boric acid, etc., is added to themelted amino condensation compound mixed and/or reacted. Othercarbonization auxiliaries may be mixed with the amino condensationcompounds to produce the flame retardant amino condensation composition.The amino condensation compounds may be further reacted with an aldehydein the presence of a neutral or basic or acidic catalyst by mixing andheating the urea condensation compound with the aldehyde, usually in anaqueous medium, to just below the boiling point of the components atambient or an elevated pressure thereby producing a ureacondensation-aldehyde resin. The amino condensation salt of phosphoruscompounds are produced by contacting the amino condensation compoundswith a phosphorus containing compound that will react with an aminocondensation compound, under conditions sufficient to prepare an aminocondensation salt of a phosphorus containing compound. Fillers andcarbonization auxiliaries may be added to the amino condensationcompounds and/or amino salt of phosphorus and/or boron containingcompounds and/or amino condensation-aldehyde resin. The aminocondensation compounds and amino condensation-aldehyde resins with orwithout carbonization auxiliaries and fillers may be reacted with oradded to or applied to a more flammable organic material.

The isocyanic acid may be reacted with itself to form biuret which isthen reacted with an alkaline solution such as alkali metal hydroxidesthen neutralized with a metal sulfate such as cupric sulfate therebyforming a biuret-metal complex, which is then heated with component B toform a flame retardant amino-metal condensation compound.

Component A

Urea is utilized as component A and may be in the form of a powder,crystals or a solid. Urea is utilized in the amount of 50-100 parts byweight.

Component B

Any suitable nitrogen containing compound, especially those containingreactive —NH₂, —COOH, —OH, —NCO, and/or epoxide radical, that will reactwith isocyanic acid and/or cyanic acid which is produced by heating ureamay be utilized in this invention. The nitrogen containing compound maybe an organic or an inorganic compound. Suitable organic nitrogencontaining compounds may be an aliphatic, aromatic, cyclic,aliphatic-aromatic or aliphatic-cyclic compound such as, but not limitedto, urea, urea derivatives for example, O-alkylureas, amino compounds,for example, melamine, melamine cyanurate, dicyandiamide, biuret,biuret-metal complex, guanidine, cyanoguanidine and aminoguanidine,ammonium carbonate, alkyl carbamates, alkyl isocyanates,polyisocyanates, sulfamic acid, ammonium sulfamate, amines, polyamines,thioureas, alkylanolamine, polyamides with free NH₂— radicals, amidines,amides, aldimines, ketimines, guanidine carbonate, amino carbonates,aminoborates, amino sulfates, thiourea, thiourea derivatives, compoundswith active NH₂— radicals, such as amino phosphate, amino salts oforganic phosphorus compounds and amino condensation salt of inorganicand organic phosphorus compounds containing active NH₂— radicals andmixtures thereof. The amino compounds are the preferred nitrogencontaining compound. The nitrogen containing compound may be utilized inthe amount of 10 to 200 parts by weight.

Component C

Any suitable carbonization auxiliaries may be utilized in thisinvention. Suitable carbonization auxiliaries are compounds that in thepresence of fire assist the formation of a carbonization foam or char,such as, additives that produce acidic components in the pyrolysismixture, such as phosphorus acids, boric acids or sulfuric acids. Theseacidic components are compounds such, for example, acids or salts, ortheir derivatives of sulfur, boron and phosphorus, such as,boron-phosphates, phosphates, and polyphosphates of ammonia, amines,polyamines, amino compounds, thioureas and alkyanolamines, but boricacid and its salts and their derivatives, organic phosphorus compoundsand their salts, halogenated organic phosphorus compounds, their saltsand their derivatives, silicon phosphorus halide compounds, their salts,and their derivatives, may also be used for this purpose. Thecarbonization auxiliaries and other flame retardant agents may be usedin quantities of 1 to 300 parts by weight. The nitrogen containing saltsof phosphorus acids are the preferred carbonization auxiliaries.

Component D

Any suitable organic material which is more flammable than the aminocondensation compounds, its salts and amino condensation-aldehyde resinmay be used in this invention. Any suitable plastic resin composition ormixtures thereof and any suitable natural organic material maybe used inthis invention and mixtures thereof. These materials may be in the formof a solid, cellular suspension, emulsion or solution. Suitable plasticresin include, but not limited to, vinyl dienes, vinyl-diene copolymers,polyesters, polyester resins, phenoplasts, aminoplasts, polyepoxyresins, polyurethanes, furans, polyamides, polyimides, polycarbonates,homopolymers of such olefins as ethylene, propylene, and butylene; blockcopolymers, consisting of optional combination of these olefins;polymers of vinyl compounds such as vinyl chloride, acrylonitrile,methyl acrylates, vinyl acetates and styrene; copolymers of theforegoing olefins with vinyl monomers, copolymers and terpolymers of theforegoing olefins, with diene compounds; polyesters such as polyethyleneterephthalate, polyester resins; polyamides such as nylon;polycarbonates, polyoxymethylene, silicones, polyethers, thioplasts,polytetrafluoroethylene, polysulfones, vinyldienes, poly(vinyl acetate),aliphatic allyl compounds, polyacrylonitrile, aliphatic dienes,polybutadiene, butadiene-acrylonitrile, butadiene-styrene copolymers,aromatic vinyl compounds, heterocyclic vinyl compounds, cyclicunsaturated compounds, urethane-epoxy resins, polyimides, urethanesilicates, cellulose nitrate rayon, regenerated cellulose film celluloseacetate, cellulose esters, cellulose ethers, cyanoethyl cellulose,chlorinated rubber and mixtures thereof.

Suitable natural products include but not limited to wood, cellulose,lignin-cellulose, paper, starch, cotton, wool, linen, dammars, copols,other natural resins, rosins, lignin, natural rubber, natural proteins,e.g., soya bean protein, silk, glues, gelatin, etc.; modified celluloseand mixtures thereof. Natural organic material and plastics may be mixedtogether. The amino condensation compounds, its salts and aminocondensation-aldehyde resin or amino condensation composition maybeutilized in the amount of 10-200 percent, percentage based on the weightof the more flammable organic material.

Component E

Suitable inorganic phosphorus compounds include, but not limited to,phosphoric acid, pyrophosphoric acid, triphosphoric acid, metaphosphoricacid, phosphorous acid, hydrophosphorous acid, phosphinic acid,phosphinous acid, phosphine oxide, phosphorus trihalides, phosphorusoxyhalides, phosphorus oxide, mono-metal hydrogen phosphates, ammoniadihydrogen phosphate, bromated phosphates, alkali metal dihydrogenphosphate and halogenated phosphate-phosphite and their halides andacids. Organic phosphorus compounds include, but not limited to, alkyl,cyclic, aryl and alkyl-aryl phosphorus compounds, such as,alkylchlorophosphines, alkyl phosphines, alkyl phosphites, dialkylhydrogen phosphites, dialkyl alkyl phosphonates, trialkyl phosphites,organic acid phosphates, organic diphosphonate esters, aryl phosphites,aryl hydrogen phosphates, halogenated phosphonates esters and mixturesthereof may be used to produce amino condensation salts of phosphoruscontaining compounds. Amino condensation borates may be produced bycontacting boric acid and amino condensation compound under conditionssufficient to prepare the amino condensation borates which may also beutilized as a flame-retardant compound. Amino condensationboron-phosphates may be produced by contacting boron-phosphates andamino condensation compounds under conditions sufficient to prepareamino condensation boron-phosphate compounds which may also be utilizedas a flame-retardant compound. The salt forming phosphorus containingcompounds will react with the amino condensation compounds to form anamino condensation salt of a phosphorus containing compound. Phosphoricacid is the preferred inorganic phosphorus containing compound. Dimethylmethyl phosphonate is the preferred organic phosphorus containingcompound. Boric acid is the preferred boron containing compound. Thephosphorus containing compound or boron containing compound orboron-phosphorus containing compounds are used in the amount of 10 to100 parts by weight.

Component F

Any suitable aldehyde may be reacted with the amino condensationcompounds. Suitable aldehydes include, but not limited to, formaldehyde,paraformaldehyde, acetoaldehyde, butyraldehyde, chloral, and other alkylaldehydes, furfural, benzyl aldehyde and other aromatic aldehydes.Aqueous formaldehyde is the preferred aldehyde. The aldehyde is used inthe amount of 10 to 100 parts by weight.

Component G

Any suitable filler may be used in this invention. The fillers that maybe utilized in the flame retardant mixture are usually insoluble in thereaction mixtures. They may be inorganic substances, such as, alkalimetal silicates, alkaline earth metal silicates, metal silicates,silica, metals and metal oxides, carbonates, sulphates, phosphates andborates, and glass beads or hollow glass beads. Hydrated aluminum oxideis preferred. They may be organic substances, such as, amino compounds,such as urea, melamine, dicyandiamide, and other cyanuric derivatives ortheir formaldehyde resins, aminophosphates, amino salts of organicphosphates, phenol-aldehyde resin powder, powdered coke, graphite,graphite compounds and mixtures thereof. The organic halide flameretardant compounds may also be added as fillers. The filler may be usedin the amount of 1 to 300 parts by weight.

Component H

Any suitable basic or acidic catalyst may be used in the reaction ofamino condensation compounds with aldehydes. Suitable basic compoundsinclude but not limited to, compounds containing alkali metal, alkalineearth metal and ammonia radicals and mixture thereof. Suitable acidiccompounds include, but not limited to, halogen acids, acidic phosphoruscontaining compounds, acidic compounds containing sulfur, sulphonic acidhalides, carboxylic acids, polycarboxylic acids, nitric acids andmixtures thereof. In some reactions basic or acidic catalytic are notnecessary. A catalytic amount is utilized and may range from the amountof 0.1 to 20 parts by weight.

ILLUSTRATIVE EMBODIMENTS

In general, the amino condensation compounds are compounds which areproduced by heating urea with other nitrogen containing compounds thatwill condensate or react with urea to produce amino condensationcompounds. The heated urea first form isocyanic acid and/or cyanic acidwhich polymerizes with itself to form biuret, cyanuric and/or cyamelide.Large molecule of cyamelide may be formed in this process.

Any amount of the amino condensation compound or the amino condensationcomposition which includes the amino condensation compound and/or itssalts and may include carbonization auxiliaries and fillers suitable forthis invention may be utilized. Preferably, flame retardant amounts ofthe amino condensation compounds and/or its salts and/or the aminocondensation-aldehyde resin or the amino condensation composition arefrom 10 percent by weight to about 200 percent by weight of theotherwise more flammable organic materials such as polyester resins,polyepoxy resins, polyurethane components, acrylic and acrylate resins,polyacrylonitrile, polystyrene, etc.

One method to measure this flame retardant capability is an oxygen indextest. By selecting the various combinations of the amino condensationcomposition to incorporate into a more flammable organic material theaverage limiting oxygen index (LOI) can be raised 10 to 30 percent ormore when compared to otherwise comparable samples without the flameretardant amino condensation compound or composition. For example theLOI of three flexible polyurethane foams with the amino condensationcomposition were raised more than 30 percent to a LOI of 31.7, 30.3 and30.7.

When the amino condensation composition were incorporated into rigidpolyurethane foam and tested with a propane torch with a 2″ flame heldagainst the lower edge of the verticle held foam for one minute, theflame did not spread, the melted foam did not bum, a char was formed,the flame went out when the torch was removed and there was very littleweight loss.

Various amino condensation compositions were incorporated into solidresins, for example, flexible polyepoxy resins, rigid polyepoxy resins,polyester laminating and flexible resin, polystyrene resin, polymethylmethyl acrylate resin, polyvinyl acetate resin, solid polyurethane,polyisoprene, acrylonitrile, etc, then tested with a propane torchhaving a 2″ flame held against the lower edge of the verticle sample forone minute, the flame did not spread, and went out when the flame wasremoved and there was very little weight loss. The said above materialwere tested without the amino condensation composition and all burned.

Various natural products such as wood shingles, paper, cotton cloth, andcardboard were coated with various amino condensation compositions in anaqueous emulsion containing 20% by weight of the powdered aminocondensation composition then after the product had dried, then theywere tested by applying a 2″ flame from a propane torch against the edgeof the products, for 1 minute and the flame did not spread whereas theuncoated products caught on fire and burned.

DESCRIPTION OF PREFERRED EXAMPLES

The present invention will now be explained herein-after by way of a fewexamples and comparative examples, these examples setting, however, nolimits to this invention. Parts and percentages are by weight, unlessotherwise indicated.

Example 1

100 parts by weight of urea is heated to above the melting point of ureaand up to about 160 degree C. for 0.1 to 1 hour. Ammonia evolves fromthe melted urea thereby producing an amino condensation compound (ureacondensation compound). The cooled amino condensation compound is groundinto a fine powder.

Example 2

100 parts by weight of urea and 50 parts by weight of melamine are mixedthen heated to above the melting point of urea and up to 160 degree C.for 0.5 to 2 hours. Ammonia evolves from the mixture thereby producingan amino condensation compound (urea-melamine condensation compound).The cooled amino condensation compound is ground into a fine powder.

Example 3

Example 2 is modified wherein 75 parts by weight of melamine is usedinstead of 50 parts by weight.

Example 4

Example 2 and 3 are modified wherein another nitrogen containingcompound is used in place of melamine and selected from the list below:

a) dicyandiamide k) biuret b) guanidine l) ammonium bicarbonate c)aminoguanidine m) methylolurea d) thiourea n) methylthiocyanate e)ethylamine o) monomelamine phosphate f) diethylamine p) urea phosphateg) ammonium carbonate q) melamine borate h) urea carbonate r) guanidinecarbonate i) diethylanolamine s) aniline j) ammonium sulfamate t)melamine cyanurate k) ethyl carbamate u) monoguanidine phosphate l)ethyl isocyanate v) acrylonitrile w) buiret-metal complex

About 100 parts by weight of the urea-melamine condensation compound ofexample 2 is mixed with 25 parts by weight of phosphoric acid (75%) thenheated to above the melting point of the urea condensation compound forabout 30 minutes there by producing a urea-melamine condensation salt ofphosphoric acid.

Example 6

Example 5 is modified by first reacting 5 parts by weight of boric acidwith the 25 parts by weight of phosphoric acid thereby producing aboron-phosphate condensation compound and utilizing it in place of thephosphoric acid in example 5.

Example 7

Example 5 is modified wherein another phosphorus containing compound isutilized in place of phosphoric acid and selected from the list below:

a) pyrophosphoric acid n) tris(2-chloropropyl) phosphate b) phosphinicacid o) triphenyl phosphite c) phosphorus trichloride p) tris2-chloroethyl phosphite d) phosphorus oxytrichloride q) triethylphosphite e) phosphorus oxide r) urea dihydrogen phosphate f) ammoniumdihydrogen s) diethyl phosphite phosphate t) trimethyl phosphite g)mono-aluminum phosphate u) dibutyl pyrophosphoric acid h) dimethylmethyl v) melamine hydrogen boron-phosphate phosphonate (DMMP) x)hypophosphorous acid i) dimethyl hydrogen y) methyl amine salt ofphosphoric acid phosphite z) O,O-dimethyl hydrogen dithiophosphate j)phenyl acid phosphate k) methylchlorophosphine l) phosphorus m)phosphorus thiochloride

Example 8

Example 1 is modified wherein a phosphorus containing compound selectedfrom the list in example 7 is added to the urea before it is heatedthereby producing a mixture of urea condensation salt of a phosphoruscontaining compound and urea salt of a phosphorus containing compound.The mixture is ground into a fine powder.

Example 9

30 parts by weight of the melted urea-melamine condensation compound ofexample 2 are added to 100 parts by weight of a polypropylene triol witha 56 hydroxyl number and a mol wt. of 3000 thereby producing a stableemulsion for use in the production of flame retardant polyurethaneproducts.

Example 10

Example 5 is modified wherein 20 parts by weight of powdered dimelaminephosphate is added to and mixed in with the melted urea condensationcompound thereby producing a flame retardant amino condensationcomposition.

Example 11

Example 3 is modified wherein 25 parts by weight of melamine powder areadded to and mixed in with the melted amino condensation compoundthereby producing a flame retardant amino condensation composition.

Example 12

100 parts by weight of urea, 50 parts by weight of melamine powder and20 parts by weight of boric oxide are mixed then heated above themelting point of urea and up to 160 degree C. for 45 minutes whileagitating. Ammonia evolves from the solution. The urea-melaminecondensation compound containing boric oxide is cooled, then ground intoa fine powder thereby producing a flame retardant amino condensationcomposition.

Example 13

100 parts by weight of urea, 30 parts by weight of dicyandiamide and 20parts by weight of boric acid are mixed then heated above the meltingpoint of urea and up to 160 degree C. for 0.5 to 1 hour. Ammonia evolvesfrom the mixture. The mixture of urea-dicyandiamide condensationcontaining urea salt of boric acid is cooled then grown into a finepowder thereby producing a flame retardant amino condensationcomposition.

Example 14

100 parts by weight of urea, 30 parts by weight of dimelamine phosphateare mixed then heated above the melting point of urea and up to 160degree C. for 40 minutes thereby producing a flame retardant aminocondensation salt of phosphate composition. After cooling it is groundinto a fine powder.

Example 15

Example 12 is modified wherein 10 parts by weight of a phosphorus saltforming compound selected from the list below is added to and reactedwith the amino condensation composition;

a) phosphoric acid h) phosphinic acid b) pyrophosphoric acid i)phosphorus oxytrichloride c) dimethyl methyl j) ammonium dihydrogenphosphate phosphonate (DMMP) k) dimethyl phosphoric acid d) dimethylhydrogen phosphite l) diethyl ethyl phosphonate e) trimethyl phosphitem) magnesium hydrogen phosphate f) phenyl acid phosphate n) monoaluminum phosphate g) phosphorus trichloride o) trichlorosiliconphosphous trichloride

Example 16

Example 2 is modified wherein 20 parts by weight of a halogenated flameretardant compound selected from the list below is mixed with thepowdered urea-melamine condensation compound thereby producing a flameretardant amino condensation composition:

a) brominated epoxy olgmer

b) decabromodiphenyl oxide

c) pentabromodiphenyl oxide

d) 2,3-dibromopropanol

e) octabromodiphenyl oxide

f) tris(dichloropropyl)phosphite

g) tris(dichloropropyl)phosphite

Example 17

Example 3 is modified wherein 20 parts by weight of a powdered fillerselected from the list below is mixed with the powdered ureacondensation compound thereby producing a flame retardant aminocondensation composition:

a) hydrated aluminum oxide o) urea phosphate powder p) silica powder b)hydrated sodium silicate powder q) phenol-formaldehyde resin powder c)melamine r) aluminum phosphate d) dicyandiamide s) thiourea e) urea t)hollow beads f) melamine phosphate u) expandable graphite g) melamineborate v) melamine salt of DMMP h) ammonium phosphate r) ammoniumsulfate i) ammonium pyrophosphate s) magnesium chloride j) ammoniumcarbonate t) antimony trioxide k) ammonium borate u) boron-phosphatepowder l) ammonium sulfamate w) melamine boron-phosphate m) guanidinepowder n) guanidine carbonate x) ammonium boron-phosphate powder y)silicon dimethyl methyl phosphate

Example 18

30 parts by weight of the urea-melamine condensation compound of example2 are mixed and reacted with 10 parts by weight of dimethyl methylphosphonate (DMMP) thereby producing an amino condensation salt of DMMPcomposition, then it was added and mixed with 60 parts by weight of aflexible polyepoxy resins with its polyamine curing agent. The resin iscured then was tested with a 2″ propane flame held against the edge ofthe sample for 1 minute. A char was formed, the flame did not spread,the flame went out when the torch was removed and there was very littleweight loss.

Example 19

30 parts by weight of the amino condensation composition of example 10are mixed with 100 parts by weight of a flexible polyester resincontaining its catalyst. The resin is cured then flame tested using apropane torch with a 2″ flame held against the edge of the sample for 1minute. A char was formed, the flame did not spread and went out whenthe torch was removed.

Example 20

30 parts by weight of the amino condensation composition of 17c isincorporated into 70 parts by weight of a flexible polyurethane foamproduced from MDI and a triol which weighs about 1.75 lbs./cu.ft. Thefoam was flame tested by using Calif. T133 Test wherein 100 gms of woodis burned on top of the foam. After burning the wood on the foam therewas a 50.5 gms weight loss. A weight loss of less than 60 gms isnecessary to pass the test.

Example 21

30 parts by weight of the amino condensation composition of example 10are incorporated in 100 parts by weight of a rigid polyurethane foam ofabout 2 lbs./cu.ft., produced using polymeric MDI and polyol. The rigidpolyurethane foam was flame tested using a propane torch that had a 2″flame and was held against the edge of the foam. A char was formed, theflame did not spread and went out when the torch was removed, and therewas very little weight loss.

Example 22

Example 14 is modified wherein another amino phosphorus containingcompounds is selected from the list below and utilized in place ofdimelamine phosphate:

a) melamine phosphate l) O-methyl urea b) dicyandiamide phosphate m)urea salt of boron- c) urea dihydrogen phosphate phosphate d) guanidinephosphate n) urea-formaldehyde e) aminoguanidine phosphate phosphate f)diethyltriamine urea phosphate o) aminophenol phosphate g) melamine saltof dimethyl methyl p) ammonium urea phosphate phosphonate q) ammoniummelamine h) melamine salt of dimethyl hydrogen phosphate phosphite r)melamine salt of trimethyl i) methylamine melamine phosphoric acidphosphite j) methyl carbamate salt of phosphoric s) melamine salt ofphenyl acid acid phosphate k) melamine salt of boron-hydrogen phosphate

Example 23

Example 1 is modified wherein the urea condensation compound is heatedand reacted with 20 percent by weight of urea, percentage based on theweight of the urea condensation compound.

Example 24

Example 4 is modified wherein the urea is first heated and reacted withitself to form a urea condensation compound then additional 20 percentby weight of urea, percentage based on the weight of the ureacondensation compound, is added with the nitrogen containing compound.

CONCLUSION

It is surprising that the amino condensation compounds greatly increasethe flame retardant properties and are comparable or better in flameretarding than urea, biuret, melamine and other amino compounds. Theaddition of the carbonization agents increases the development of aninsulating carbon char which helps the materials to resist furtherdegradation and thereby further exposure to flame. A plastic foam forexample, which contains this amino condensation composition resistmelting when exposed to heat. The melted drippings of the material beingflame tested is reduced, and any burning is minimized. There is aminimum amount of smoke given off these flame retardant materials whenflame tested.

These flame retardant amino condensation compounds and compositions,amino condensation salts of phosphorus and/or boron containing compoundsand amino condensation-aldehyde resins has many uses such as being addedto adhesives in the production of pressed wood, plywood, chipboard,etc., in flame retardant paints and varnishes, for flame retardingplastics and polyurethane foams and reacts with aldehyde to produceuseful resins.

It will be appreciated by those skilled in the Arts that changes andmodifications of the preferred embodiments can be made without departingfrom the spirit and broader aspects of the invention as set forth in theappended claims.

I claim:
 1. A flame retardant composition produced by incorporating aflame retardant amino condensation composition in an organic material,under reaction or mixing conditions and in an amount sufficient toreduce the combustibility of the organic material, said aminocondensation composition produced by mixing and heating the followingcomponents: (A) urea, in the amount of 50 to 100 parts by weight; (B)nitrogen containing compound that condensate and/or react with isocyanicacid and/or cyanic acid, in the amount of 10 to 300 parts by weight;components A and B are mixed then heated to above the melting point ofurea thereby converting the melted urea into isocyanic acid and/orcyanic acid which reacts with urea and component B thereby producing anamino condensation compound; then the following components are added andmixed (C) carbonization auxiliaries; (D) filler; thereby producing anamino condensation composition.
 2. A flame retardant composition ofclaim 1 wherein the nitrogen containing compound that condensate and/orreact with isocyanic acid and/or cyanic acid, produced by heating 50 to100 parts by weight of urea, is selected from the group consisting ofamino compounds, amines, polyamines with reactive —NH₂ radicals, biuret,biuret-metal complex, thiourea, guanidine carbonate, ammonium carbonate,urea carbonates and mixtures thereof; in the amount of 10 to 300 partsby weight.
 3. The flame retardant composition of claim 1 wherein thecarbonization auxiliaries are selected from the group consisting ofphosphorus containing compounds, boron containing compounds,boron-phosphorus containing compounds, silicon-phosphorus containingcompounds and sulfur containing compounds that produce acidic componentsin the pyrolysis mixture; in the amount of 1 to 300 parts by weight. 4.The flame retardant composition of claim 1 wherein the filler isselected from the group consisting of urea, melamine, dicyandiamide,melamine cyanurate, amino phosphates, aminopolyphosphates, aminoplasts,phenoplasts, powdered synthetic resins, sawdust, carbohydrates,bituminous additives, graphite, graphite compounds, powdered coke,silica, alkali metal silicates, alkaline earth metal silicates, metals,and metal silicates, oxides, carbonates, sulphates, phosphates andborates, glass beads, hollow glass beads, hydrated aluminum oxide andmixtures thereof; in the amount of 1 to 300 parts by weight.
 5. Theflame retardant composition of claim 1 wherein an aldehyde, in theamount of 10 to 100 parts by weight, is reacted with the aminocondensation compound of claim 1 thereby producing an amino-aldehydecondensation compound.
 6. The flame retardant composition of claim 1wherein component B, a nitrogen containing compound, is urea.
 7. Theflame retardant composition of claim 1 wherein component B, a nitrogencontaining compound, is melamine.
 8. The flame retardant composition ofclaim 1 wherein component B, a nitrogen containing compound, isdicyandiamide.
 9. The flame retardant composition of claim 1 whereincomponent C, the carbonization auxiliaries, is a phosphorus containingcompound and is reacted with the amino condensation compound therebyproducing an amino condensation salt of phosphorus containing compound,and is utilized as the amino condensation composition.
 10. The flameretardant composition of claim 9 wherein the phosphorus containingcompound is an acidic phosphorus compound.
 11. The flame retardantcomposition of claim 9 wherein the phosphorus containing compound is anorganic phosphorus containing compound.
 12. The flame retardantcomposition of claim 1 wherein the amino condensation composition isutilized in an amount of 10 to 200 percent by weight, percentage basedon the weight of the organic material to be flame retarded.
 13. Theflame retardant amino condensation composition of claim 1 whereincomponent B, a nitrogen containing compound, is urea carbonate.
 14. Theflame retardant composition of claim 11 wherein the organic phosphoruscompound is dimethyl methyl phosphonate.
 15. The flame retardantcomposition of claim 10 wherein the acidic phosphorus compound isphosphoric acid.
 16. A method for reducing combustibility of organicmaterial comprising incorporating an amino condensation compound and/orcomposition with the organic material, under reaction and/or mixingconditions of the organic material, said amino condensation compositionproduced by the method comprising of mixing and heating, the followingcomponents: (A) urea, in the amount of 50 to 100 parts by weight; (B)nitrogen containing compound that condensate and/or react with isocyanicacid and/or cyanic acid produced by heating a urea compound, in theamount of 10 to 300 parts by weight; components A and B are mixed thenheated to above the melting point of urea thereby converting the urea toisocyanic acid and cyanic acid which are reacted with urea and componentB thereby producing an amino condensation compound; then add and mixcomponents (C) carbonization auxiliaries, in the amount of 1 to 300parts by weight; (D) filler, in the amount of 1 to 300 parts by weight;thereby producing a flame retardant amino condensation composition. 17.The product produced by the method of claim
 16. 18. A flame retardantcomposition produced by incorporating an amino condensation compound ina more flammable organic material, under reaction and/or mixingconditions and in an amount sufficient to reduce the combustibility ofthe more flammable organic material, said amino condensation compound isproduced by mixing urea with an nitrogen containing compounds thenheating the mixture to above the melting point of urea therebyconverting the melted urea to isocyanic acid and cyanic acid whichreacts with the urea, urea condensation compound and nitrogen containingcompound.
 19. The flame retardant composition of claim 1 wherein theflame retardant composition is a polyurethane material incorporated withan amino condensation composition of claim
 1. 20. The flame retardantcomposition of claim 1 wherein Component A is first heated to form acondensation compound then reacted with Component B.
 21. The flameretardant amino condensation composition produced by the process ofclaim 1.